US3222119A - Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone - Google Patents

Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone Download PDF

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Publication number
US3222119A
US3222119A US798339A US79833959A US3222119A US 3222119 A US3222119 A US 3222119A US 798339 A US798339 A US 798339A US 79833959 A US79833959 A US 79833959A US 3222119 A US3222119 A US 3222119A
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sulfone
bis
beta
weight
textile materials
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US798339A
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Tashlick Irving
Scott H Foster
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Monsanto Co
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Monsanto Co
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Priority to DENDAT1414494 priority Critical patent/DE1414494A1/de
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Priority to US798339A priority patent/US3222119A/en
Priority to ES0255967A priority patent/ES255967A1/en
Priority to DE19601419494 priority patent/DE1419494A1/en
Priority to GB8453/60A priority patent/GB936479A/en
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
    • D06M13/272—Unsaturated compounds containing sulfur atoms
    • D06M13/278—Vinylsulfonium compounds; Vinylsulfone or vinylsulfoxide compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/02—Vinyl sulfones and precursors thereof

Definitions

  • This invention relates to modified cellulosic textile materials. More particularly, the invention relates to a method of treating cellulosic textile materials to improve their properties of dimensional stability, wash-and-wear, and wrinkle recovery without imparting a tendency toward chlorine retention after bleaching.
  • treating agents have been found useful for improving the dimensional stability and wrinkle recovery of cellulosic textile materials.
  • the treating agents which are known to be effective in this application usually have oneor more of the "following undesirable features: toxicity, expense, or relative inefficiency of the treating agent, instability to hydrolysis and heat, tendency toward chlorine retention when the treated material is bleached, development of objectionable odors in the treated material, yellowing with aging, yellowing on exposure to heat of an iron, or yellowing on treatment with hypochlorite bleach.
  • One object of this invention is to provide means for improving the dimensional stability and wrinkle recovery of cellulosic textile materials.
  • Another object is to provide such means by the use of treating agents which lack the aforementioned undesirable features of the treating agents previously known to be effective in improving the dimensional stability and wrinkle recovery of cellulosic textile materials.
  • Example I An aqueous solution of 10% by weight of bis(betahydroxyethyl)sulfone and 3% by weight of sodium carbonate (both percentages based on the total weight of the solution) is padded on a cotton print cloth having a count of 80 x 80 to deposit in the cloth 10% by Weight of the sulfone, based on the weight of the untreated cloth. The cloth is then dried at 220 F. for 3 minutes and cured at 310 F. for 4 minutes.
  • the treated cloth has a wrinkle recovery of 259 (warp plus filling), as determined by ASTM test method D1295 531", compared to a wrinkle recovery of 100 (warp plus filling) determined on the untreated cloth.
  • the treated cloth is washed in accordance with AATCC Standard Test Method 14-1953 with the following exceptions: (1) the process is run continuously for 120 minutes instead of 60, with a 100 minute wash cycle, (2) sufiicient sodium carbonate is added to obtain a pH of 10, (3) steam is injected continuously through the wash cycle to maintain the temperature at 212 F., and (4) the temperature of the first rinse is 160 F. After having been washed according to this procedure and dried, the treated fabric has a wrinkle recovery of 241 (warp plus filling). There is no further loss in Wrinkle recovery of the treated fabric after four subsequent washings according to the same procedure. The treated fabric shows less shrinkage after washing than the untreated fabric.
  • the treated fabric is subjected to AATCC Tentative Test Method 69-1958.
  • the test shows essentially no damage to the fabric by retained chlorine.
  • Example 11 An aqueous solution of 6% by weight of bis(-beta methoxyethyDsulfone and 3% by weight of sodium carbonate (both percentages based on the totalweight of the solution) is padded on a cotton print cloth having a count of x 80 to deposit in the cloth 5% by weight of the sulfone, based on the weight of the untreated cloth. The cloth is then dried at 200 F. for 3 minutes and cured at 320 F. for 3 minutes.
  • the treated fabric is washed for 10 minutes at F. with an aqueous solution of 0.01% by weight of an alkyl aryl sulfonate detergent and 0.01% by weight of tetrasodium pyrophosphate (both percentages based on the total weight of the solution), rinsed at 100 'F. for 10 minutes, and then rinsed again at 100 F. for 10 minutes.
  • the treated fabric shows less shrinkage after washing than the untreated fabric and has a wrinkle recovery of 184 (warp plus filling), as determined by ASTM test method D1295-53T, compared to a wrinkle recovery of 100 (warp plus filling) determined on the untreated cloth.
  • the treated fabric is subjected to AATCC Tentative Test Method 69-1958.
  • the test shows essentially no damage to the fabric by retained chlorine.
  • Example III An aqueous solution of 8% by weight of bis(betamethoxyethyl)sulfone and 1% by weight of sodium hydroxide (both percentages based on the total weight of the solution) is padded on a cotton print cloth having a count of 80 x 80 to deposit in the cloth about 7% by Weight of the sulfone, based on the weight of the untreated cloth. The cloth is then dried at 200 F. for 3 minutes and cured at 320 F. for 3 minutes.
  • the treated cloth is washed for 10 minutes at 100 F. with an aqueous solution of 0.01% by weight of an alkyl aryl sulfonate detergent and 0.01% by weight of tetrasodium pyrophosphate (both percentages based on the total weight of the solution), rinsed at 100 'F. for 10 minutes, and then rinsed again at 100 F. for 10 minutes.
  • the treated fabric shows less shrinkage atfer washing than the untreated fabric and has a wrinkle recovery of 200 (warp plus filling), as determined by ASTM test method D1295-53T, compared to a wrinkle recovery of 100 (warp plus filling) determined on the untreated cloth.
  • the treated fabric is subjected to AATCC Tentative Test Method 694958.
  • the test shows essentially no damage to the fabric by retained chlorine.
  • the textile materials which are treated by the process of this invention are materials containing cellulosic hydroxyl groups, e.g., cotton, rayon, and linen. They may be treated as fabrics or as yarns from which the fabrics are woven.
  • the water-soluble compounds with which the oellulosic textile materials are treated to improve their properties of dimensional stability and wrinkle recovery are com compounds corresponding to the general formula:
  • the amount of water-soluble sulfone treating agent incorporated into the textile material may vary from about 120% by Weight, based on the weight of the untreated textile material.
  • the amount of water in the treating bath may be varied for ease of operation in incorporating this amount of the treating agent into the textile material.
  • Suitable catalysts are the strongly basic catalysts such as the hydroxides, carbonates, and phosphates of alkali metals, i.e., Li, Na, K, Rb, and Cs; especially preferable are sodium or potassium carbonate and sodium or potassium hydroxide.
  • the aqueous treating bath should contain about 0.55% preferably 13%, by weight of alkaline catalyst, based on the total weight of the bath.
  • the process of the invention comprises impregnating a cellulosic textile material with an aqueous solution of the water-soluble sulfone treating agent and an alkaline catalyst, drying the impregnated material, and curing to react the treating agent with the textile material.
  • Impregnation of the textile material with the treating bath can be effected by any of the impregnation techniques commonly used in the textile industry, eflicaciously by padding.
  • the impregnated material may be dried at room temerature or at elevated temperatures below curing temperature. Curing is accomplished by heating the dried fabric at temperatures in the range of 250-400 F. for about 4 0.5-20 minutes, preferably by heating at 300-350 F. for 1-3 minutes, to react the treating agent with the textile material.
  • the treated textiles obtained by the process of the invention have improved properties of dimensional stablility and wrinkle recovery, do not show a tendency toward chlorine retention after bleaching, and do not lose their improved properties when subjected to acid or alkaline hydrolysis.
  • a process which comprises impregnating a cellulosic textile material containing cellulosic hydroxyl groups with an aqueous solution of an alkaline catalyst and bis(betamethoxyethyDsulfone.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Description

United States Patent PROCESS FOR TREATING CELLULOSIC TEXTILE MATERIALS WITH BIS(BETA-METHOXYETHYL) SULFONE Irving Tashlick, Springfield, and Scott H. Foster, Longmeadow, Mass., assignors to Monsanto Company, a corporation of Delaware No Drawing. Filed Mar. 10, 1959, Ser. No. 798,339
1 Claim. (Cl. 8-116) This invention relates to modified cellulosic textile materials. More particularly, the invention relates to a method of treating cellulosic textile materials to improve their properties of dimensional stability, wash-and-wear, and wrinkle recovery without imparting a tendency toward chlorine retention after bleaching.
Various treating agents have been found useful for improving the dimensional stability and wrinkle recovery of cellulosic textile materials. However, the treating agents which are known to be effective in this application usually have oneor more of the "following undesirable features: toxicity, expense, or relative inefficiency of the treating agent, instability to hydrolysis and heat, tendency toward chlorine retention when the treated material is bleached, development of objectionable odors in the treated material, yellowing with aging, yellowing on exposure to heat of an iron, or yellowing on treatment with hypochlorite bleach.
One object of this invention is to provide means for improving the dimensional stability and wrinkle recovery of cellulosic textile materials.
Another object is to provide such means by the use of treating agents which lack the aforementioned undesirable features of the treating agents previously known to be effective in improving the dimensional stability and wrinkle recovery of cellulosic textile materials.
These and other objects are attained by treating a cellulosic textile material with a water-soluble bis(betahydroxyalkyl)sulfone or bis(beta-alkoxyalkyl)sulfone in the presence of an alkaline catalyst.
The following examples are given to illustrate the invention.
Example I An aqueous solution of 10% by weight of bis(betahydroxyethyl)sulfone and 3% by weight of sodium carbonate (both percentages based on the total weight of the solution) is padded on a cotton print cloth having a count of 80 x 80 to deposit in the cloth 10% by Weight of the sulfone, based on the weight of the untreated cloth. The cloth is then dried at 220 F. for 3 minutes and cured at 310 F. for 4 minutes.
The treated cloth has a wrinkle recovery of 259 (warp plus filling), as determined by ASTM test method D1295 531", compared to a wrinkle recovery of 100 (warp plus filling) determined on the untreated cloth.
The treated cloth is washed in accordance with AATCC Standard Test Method 14-1953 with the following exceptions: (1) the process is run continuously for 120 minutes instead of 60, with a 100 minute wash cycle, (2) sufiicient sodium carbonate is added to obtain a pH of 10, (3) steam is injected continuously through the wash cycle to maintain the temperature at 212 F., and (4) the temperature of the first rinse is 160 F. After having been washed according to this procedure and dried, the treated fabric has a wrinkle recovery of 241 (warp plus filling). There is no further loss in Wrinkle recovery of the treated fabric after four subsequent washings according to the same procedure. The treated fabric shows less shrinkage after washing than the untreated fabric.
The treated fabric is subjected to AATCC Tentative Test Method 69-1958. The test shows essentially no damage to the fabric by retained chlorine.
7 Example 11 An aqueous solution of 6% by weight of bis(-beta methoxyethyDsulfone and 3% by weight of sodium carbonate (both percentages based on the totalweight of the solution) is padded on a cotton print cloth having a count of x 80 to deposit in the cloth 5% by weight of the sulfone, based on the weight of the untreated cloth. The cloth is then dried at 200 F. for 3 minutes and cured at 320 F. for 3 minutes.
The treated fabric is washed for 10 minutes at F. with an aqueous solution of 0.01% by weight of an alkyl aryl sulfonate detergent and 0.01% by weight of tetrasodium pyrophosphate (both percentages based on the total weight of the solution), rinsed at 100 'F. for 10 minutes, and then rinsed again at 100 F. for 10 minutes.
The treated fabric shows less shrinkage after washing than the untreated fabric and has a wrinkle recovery of 184 (warp plus filling), as determined by ASTM test method D1295-53T, compared to a wrinkle recovery of 100 (warp plus filling) determined on the untreated cloth.
The treated fabric is subjected to AATCC Tentative Test Method 69-1958. The test shows essentially no damage to the fabric by retained chlorine.
Example III An aqueous solution of 8% by weight of bis(betamethoxyethyl)sulfone and 1% by weight of sodium hydroxide (both percentages based on the total weight of the solution) is padded on a cotton print cloth having a count of 80 x 80 to deposit in the cloth about 7% by Weight of the sulfone, based on the weight of the untreated cloth. The cloth is then dried at 200 F. for 3 minutes and cured at 320 F. for 3 minutes.
The treated cloth is washed for 10 minutes at 100 F. with an aqueous solution of 0.01% by weight of an alkyl aryl sulfonate detergent and 0.01% by weight of tetrasodium pyrophosphate (both percentages based on the total weight of the solution), rinsed at 100 'F. for 10 minutes, and then rinsed again at 100 F. for 10 minutes. The treated fabric shows less shrinkage atfer washing than the untreated fabric and has a wrinkle recovery of 200 (warp plus filling), as determined by ASTM test method D1295-53T, compared to a wrinkle recovery of 100 (warp plus filling) determined on the untreated cloth.
The treated fabric is subjected to AATCC Tentative Test Method 694958. The test shows essentially no damage to the fabric by retained chlorine.
The textile materials which are treated by the process of this invention are materials containing cellulosic hydroxyl groups, e.g., cotton, rayon, and linen. They may be treated as fabrics or as yarns from which the fabrics are woven.
The water-soluble compounds with which the oellulosic textile materials are treated to improve their properties of dimensional stability and wrinkle recovery are com compounds corresponding to the general formula:
hydroxyethyl) sulfone, bis (beta-methoxyethyl) sulfone, bis- (bet-a-ethoxyethyl)sulfone, bis(alpha-methyl, beta-hydroxyethyl)sulfone, bis(alpha,beta,beta-trimethyl, beta-hydroxyethyl)sulfone, bis(beta-ethyl, beta-hydroxyethyl)sulfone, etc. The amount of water-soluble sulfone treating agent incorporated into the textile material may vary from about 120% by Weight, based on the weight of the untreated textile material. The amount of water in the treating bath may be varied for ease of operation in incorporating this amount of the treating agent into the textile material.
Treatment of the cellulosic textile materials with the water-soluble sulfone treating agents is accomplished in the presence of an alkaline catalyst. Suitable catalysts are the strongly basic catalysts such as the hydroxides, carbonates, and phosphates of alkali metals, i.e., Li, Na, K, Rb, and Cs; especially preferable are sodium or potassium carbonate and sodium or potassium hydroxide. The aqueous treating bath should contain about 0.55% preferably 13%, by weight of alkaline catalyst, based on the total weight of the bath.
The process of the invention comprises impregnating a cellulosic textile material with an aqueous solution of the water-soluble sulfone treating agent and an alkaline catalyst, drying the impregnated material, and curing to react the treating agent with the textile material. Impregnation of the textile material with the treating bath can be effected by any of the impregnation techniques commonly used in the textile industry, eflicaciously by padding. The impregnated material may be dried at room temerature or at elevated temperatures below curing temperature. Curing is accomplished by heating the dried fabric at temperatures in the range of 250-400 F. for about 4 0.5-20 minutes, preferably by heating at 300-350 F. for 1-3 minutes, to react the treating agent with the textile material.
The treated textiles obtained by the process of the invention have improved properties of dimensional stablility and wrinkle recovery, do not show a tendency toward chlorine retention after bleaching, and do not lose their improved properties when subjected to acid or alkaline hydrolysis.
It is obvious that many variations may be made in the products and processes set forth above without departing from the spirit and scope of this invention.
What is claimed is:
A process which comprises impregnating a cellulosic textile material containing cellulosic hydroxyl groups with an aqueous solution of an alkaline catalyst and bis(betamethoxyethyDsulfone.
References Cited by the Examiner UNITED STATES PATENTS 2,524,399 10/1950 Schoene et al. 8l16 2,539,704 1/1951 Schoene et al. 8116 X 2,670,265 2/ 1954 Heyna et al 81 20 X 2,933,367 4/1960 Reeves et al. 8120 X FOREIGN PATENTS 779,781 7/1957 Great Britain.
NORMAN G. TORCHIN, Primary Examiner.
WILLIAM B. KNIGHT, SAM ROSEN, MORRIS O.
WOLK, Examiners.
US798339A 1959-03-10 1959-03-10 Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone Expired - Lifetime US3222119A (en)

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DENDAT1414494 DE1414494A1 (en) 1959-03-10
US798339A US3222119A (en) 1959-03-10 1959-03-10 Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone
ES0255967A ES255967A1 (en) 1959-03-10 1960-02-23 Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone
DE19601419494 DE1419494A1 (en) 1959-03-10 1960-03-10 Method of treating cellulosic textile material
GB8453/60A GB936479A (en) 1959-03-10 1960-03-10 Treatment of cellulosic textile materials

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3338661A (en) * 1964-10-28 1967-08-29 Dow Corning Cellulosic fabrics rendered crease resistant and water repellant through treatment with compositions comprising catalyst-water repellant silicones and sulfone crosslinking agents
US3477802A (en) * 1963-03-19 1969-11-11 Stevens & Co Inc J P Modification of cellulose,polyvinyl alcohol and starch with compounds characterized by ethylene radicals having an electron attracting group which stabilizes carbanions on one carbon atom thereof and an alkoxy or hydroxy group on the other
US3492080A (en) * 1962-06-12 1970-01-27 Stevens & Co Inc J P Reaction of polymeric materials containing reactive hydrogen with monofunctional beta-oxyethyl sulfones
US3498736A (en) * 1961-03-20 1970-03-03 Gaf Corp Inhibiting cellulose fiber yellowing in alkaline processing at elevated temperatures through utilization of boron salts
US3501260A (en) * 1964-03-18 1970-03-17 Stevens & Co Inc J P Polyvinyl alcohol and starch bound to cellulosic textile substrate through reaction with beta-oxyethyl sulfones

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3359061A (en) * 1961-12-19 1967-12-19 Clark M Welch Process for making alkoxyethylsulfonylethyl ethers of cellulose
US3230031A (en) * 1962-02-06 1966-01-18 Clark M Welch Process for making aryloxyethylsul-fonylethyl ethers of cellulose

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2524399A (en) * 1948-07-07 1950-10-03 Us Rubber Co Cellulose treated with di-vinyl sulfone to shrinkproof
US2539704A (en) * 1948-07-07 1951-01-30 Us Rubber Co Treatment of hydroxylated polymers
US2670265A (en) * 1954-02-23 Process
GB779781A (en) * 1952-06-09 1957-07-24 Hoechst Ag Water insoluble dyestuffs and a process for producing fast dyeings and prints therewith
US2933367A (en) * 1957-10-29 1960-04-19 Wilson A Reeves Flame-resistant cellulosic textiles and process of reacting cellulose ether textiles with aziridinyl phosphine oxide or sulfide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2670265A (en) * 1954-02-23 Process
US2524399A (en) * 1948-07-07 1950-10-03 Us Rubber Co Cellulose treated with di-vinyl sulfone to shrinkproof
US2539704A (en) * 1948-07-07 1951-01-30 Us Rubber Co Treatment of hydroxylated polymers
GB779781A (en) * 1952-06-09 1957-07-24 Hoechst Ag Water insoluble dyestuffs and a process for producing fast dyeings and prints therewith
US2933367A (en) * 1957-10-29 1960-04-19 Wilson A Reeves Flame-resistant cellulosic textiles and process of reacting cellulose ether textiles with aziridinyl phosphine oxide or sulfide

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3498736A (en) * 1961-03-20 1970-03-03 Gaf Corp Inhibiting cellulose fiber yellowing in alkaline processing at elevated temperatures through utilization of boron salts
US3492080A (en) * 1962-06-12 1970-01-27 Stevens & Co Inc J P Reaction of polymeric materials containing reactive hydrogen with monofunctional beta-oxyethyl sulfones
US3477802A (en) * 1963-03-19 1969-11-11 Stevens & Co Inc J P Modification of cellulose,polyvinyl alcohol and starch with compounds characterized by ethylene radicals having an electron attracting group which stabilizes carbanions on one carbon atom thereof and an alkoxy or hydroxy group on the other
US3501260A (en) * 1964-03-18 1970-03-17 Stevens & Co Inc J P Polyvinyl alcohol and starch bound to cellulosic textile substrate through reaction with beta-oxyethyl sulfones
US3338661A (en) * 1964-10-28 1967-08-29 Dow Corning Cellulosic fabrics rendered crease resistant and water repellant through treatment with compositions comprising catalyst-water repellant silicones and sulfone crosslinking agents

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GB936479A (en) 1963-09-11
ES255967A1 (en) 1960-04-16
DE1419494A1 (en) 1968-10-10

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